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Supporting image for The Art of Interviewing: Getting the Most from Your Guests – @RobCaldwell207
The Art of Interviewing: Getting the Most from Your Guests – @RobCaldwell207
The Agents of Change

If you’re looking to start a webinar or podcast, for example, incorporating interviews into the mix is a great way to broaden your audience and increase traffic, among other great benefits. But if you have no experience as an interviewer, there are a few key tips that you should keep in mind that will help even a rookie interviewer navigate their way from start to finish.

When you have over 30 years of broadcasting experience under your belt like Rob Caldwell does, you learn a thing or two about how to do a successful interview. But success comes from practice and learning from the not so successful ones. Today Rob shares some of his experiences and tips to help you get on your way to becoming a great interviewer.

Rich: Rob Caldwell has worked as a reporter and anchor at WCSH, the NBC station in Portland, Maine, for more than 30 years. He is the co-anchor of the 5:30 PM newscast and of 207, the news magazine program that has aired weeknights since 2003. During that time he’s interviewed thousands of people from Andre the Giant to Barack Obama, from George Takei to Doris Kearns Goodwin. Rob, by the way, I notice there’s no mention of Rich Brooks on this, but we’ll get back to that later.

Rob: There are thousands. I couldn’t get you in. 

Rich: Ok, understood. Since 2004 he has ridden a motorcycle across the U.S. a dozen times. His longest motorcycle trip was 8 weeks, more than 10,000 miles, and he managed to survive without so much as a computer, watch or alarm clock. Rob, welcome to the show.

Rob: Thank you, Rich, delighted to be here.

Rich: For those of you that don’t know, this is my opportunity to turn the tables on Rob, because very often I am the “tech guru” on 207 and Rob usually asks me questions. So I figured it was time to have him on my show.

Rob: Usually the questions that I ask of you are fairly elementary because my knowledge of technology is so limited. So it needs to be pointed out that you are an exceedingly kind guest when you come on 207, and you sort of take me by the hand and guide me along the path instead of the other way around.

Rich: Well I’m just glad for the opportunity to come on 207, it is always fun. Now what was the impetus for you to get into broadcasting in the first place?

Rob: I actually got into broadcasting because I was interested in news and I liked to write. Those were the two kinds of things that drove me, although I was always interested in the idea of talking to people. Radio in particular I thought was really intriguing. I never did it when I was in college at a college radio station or anything like that. I kind of did not know what I wanted to do when I was in college, and then when I got out of college I drove a cab for a little while, and I was a bellhop, I was a substitute teacher.

And then finally my focus sharpened – probably out of desperation – and I got a job as an unpaid intern at a radio station and I was just playing the music. They hadn’t got automated yet, so I was playing music but never on the air. But then they started letting me do stuff in the newsroom and I really loved it right from the start.

Rich: Alright, that’s cool. Now one of the reasons I wanted to have you on the show is that a lot of our audience create content as part of their job, and interviews are a great way to create content. So, do you enjoy the interview process? I mean, it sounds like you enjoy talking to people, is it the same thing?

Rob: It’s very similar but not quite exactly the same thing. If you don’t enjoy talking to people, then I can’t imagine how you’re ever going to do well as an interviewer. So you’ve got to have that. It’s not just a conversation, because when we talk to people and sit down over a cup of coffee and chat with someone – whether it’s someone you’ve known for a long time or someone you’ve just met – and if you find that person interesting, then the conversation is going to wander in all sorts of directions without any structure. And it will still be great, it can be a blast it can be a wonderful time.

But an interview that is unstructured and wanders in any direction at any given time might not be the best experience for the listener. And that’s what you want to do is you want to be paying attention to what your listener is going to get out of it.

Rich: So how do you then prepare for these interviews to make sure that they’re not just meandering paths that might be dinner with Andre, and actually end up delivering something of value?

Rob: Well one thing you want to do is you want to know something about the person that you’re talking to. You need to have some of the basic biographical information, more than just the basics, you want to dig in and learn something about that person. Where did that person grow up, where did they go to school, what did that person do for his or her first job, how did that person get to where he or she is now, where has that person had failure in life, does that person come from a family of 13 kids, is that person an only child? All that kind of stuff, it’s all something that you start with. So that’s where you begin is by finding out information about the person you’re talking to.

And then from there you go to maybe the professionals, you talk to someone because that person has just invented the hottest new app. Then you look at the professional background that person has, and the professional arena in which that person is operating. Preparation is job one.

Rich: How much time do you ever look at precious interviews that this person has done, if that’s applicable?

Rob: I do, I look at YouTube videos. And if they’re good ones, I find them very helpful. A lot of people that I interview have never been interviewed before on television or on a podcast, or anywhere. They’re just regular folks who we have on because they’re doing something interesting in Maine, but they haven’t made a big splash in the world of entertainment or technology or politics. A lot of them are just regular people, they’ve never been interviewed. So when you have someone like that, you’ve still got to prepare and find out something about them.

On the other hand, if you’re talking to someone that’s really famous and really well known who’s done dozens or hundreds of interviews, you have a whole other set of challenges, which we can talk about later.

Rich: Well let’s start with maybe the people who do not have as much experience and maybe you ask them a question and they say, “Yup.”, “Nope”. How do you get them to open up? Is that a challenge with maybe somebody who doesn’t have a lot of experience being interviewed?

Rob: Ask them about something they love. Ask them about something that they really know about. If you’re talking to someone that doesn’t have a lot of experience being interviewed, but the person is really passionate about what he or she does. Let’s say you’re a dog groomer that has never been interviewed before, but if we start out the interview by me saying, “Tell me about the first pet you ever had”, that might not be a bad way to begin, because that person was 4 years old and had a collie and loved that and got crazy about dogs ever since then and turned it into a pet groomer. That’s a good way to start.

So again, my questions of “tell me what you love about what you do”, puts some kind of a little spin on it – a little twist – and that’s a good way to get started and get people talking.

Rich: Well now I wish I had asked you who your first interview was. But whatever, we can skip around. So let’s talk about when somebody is established. Because a lot of people who are doing podcasts like mine, they’re looking to get in front of influencers. The influencer is his or her own audience, as well as it’s a great opportunity for us to connect with influencers. And very often these influencers have been asked the same questions a million times over the years in interviews. How do we get them to share something fresh, or is that even a viable option?

Rob: No, that’s a good question. Let me ask you a quick question, Rich, who is your dream get, who would you really like to interview?

Rich: That’s a great question. So one of the people on my list would be Sally Hogshead, who wrote the book, Fascinate, as well as a few other books.

Rob: Ok, Sally has been interviewed dozens – maybe hundreds – of times, I’m guessing. Correct?

Rich: Absolutely.

Rob: The best advice that I ever got about this came from – oddly enough – Barbara Walters, who has a reputation for being one of the most skilled interviewers in television. She’s not everyone’s cup of tea, but she was darn good. I got to interview here a few years ago when she published her memoire, which was a big book, about 600-700 pages. And I read the whole thing and that served me well, because for nothing else I got one, great tip out of that. Her tip on how to interview people that have been interviewed hundreds of times. And the reason people have been interviewed hundreds of times is because they’re famous or they’re accomplished.

They can come from any field, but the advice that she gave – whether it’s a baseball player, a technology guru, or a politician, or an actor – it doesn’t matter who that person is, ask them something about his or her childhood. Something about that person’s life before that person became rich and famous and universally known. People love to talk about their childhoods – most of them – if they had a dismal childhood, then maybe not. But most people will talk about their childhoods, and that was a more innocent way, before they were famous and everybody didn’t want a piece of their time, everyone didn’t know them when they walked into a coffee shop. That’s a great way to talk to someone who’s been interviewed hundreds of times before, a great way to get started.

Rich: Now most of your interviews when you’re interviewing people on TV last 5-10 minutes, would you say?

Rob: Yeah, what appears on air is 5-6 minutes. When I’m doing a live interview, that’s how long it’s going to run, 5-6 minutes. When I do a taped interview that is later edited, I usually talk to people for maybe 10-20 minutes, and it’s then edited down to about 5.

Rich: Ok, because I think the only thing they have ever edited for me is I think one time I said something that could have been construed in a completely non-innocent way, and they said for my own sake they were just going to edit that piece out. But you and I pretty much go straight up.

So the kind of questions that you might ask in terms of childhood, that may be left on the cutting room floor, if you end up doing some editing for your show.

Rob: It might, it all depends on what they say. But the key think is it gets them started and it loosens them up. So we always think of actors getting interviewed a lot, they’re on every late night show, they come on and pimp their movie and the interviewer will say, “Tell me about your new movie ‘Genesis Warlock 7’”. Wow, this topic is going to be great. I do not give a damn about ‘Genesis Warlock 7’, but I might be interested in the first acting class that person ever took or first school play that person ever appeared in. So that’s why those childhood questions can really get things going.

Rich: Interesting. Alright, I might try working that into some future interviews. Now do you have some “go to” questions that you always have in your back pocket that you ask almost everybody, questions that always seem to get a good answer?

Rob: I have some “go to” questions; they’re usually the ones that say, “break glass in case of emergency”. If I feel like the interview is really flopping then I’ll go with them. Here’s one that I will use on accomplished people, and that is that I will ask them about their failures and setbacks, things they did that did not work out and what they learned from those. It’s not the most original question in the world, but it can sometimes help jumpstart an interview that may be not giving me much. Because successful people – oddly enough – are usually not reluctant to talk about their failures and what they learned from it, because they feel a certain pride in the fact that they did overcome it. So that’s not a bad question when you’re just not really feeling like you’re getting any traction.

Rich: So you obviously have met so many people over the years, who was the best interview you ever had and why?

Rob: The best interview I ever had was – this is obscure – but he was an entertainer from a group called The Hudson Brothers. Weirdly enough they had a variety and musical TV show back in the 70’s. And one of the brothers had a relationship with Goldie Hawn, and so his daughter is Kate Hudson. But the guy that I talked to was Mark Hudson; he was a musician and a producer and had been around in the music world. Man, he was funny and had a million stories, he was a mimic, and he did great accents. He could go anywhere and he was just a marvelously entertaining storyteller. Just great. I could have sat and talked to that guy for a week, he was terrific.

Rich: Hmm, I’ll have to go check that out. Now obviously you don’t have to mention names here – but if you do, that will be that more juicy – out of all the people you’ve interviewed, who was probably the worst interview you ever had?

Rob: The worst interview I ever had – I had not been in television news that long – and I was anchoring our Sunday noon news. Which in terms of resources was not #1 on the priority list. So every week we would do a local interview and it would run about 5 minutes. These were not scintillating interviews that were immediately sent off to the Museum of Broadcasting, I can assure you.

So one week we had a guy come on who was going to talk about something new in the Maine Court System which was an emphasis on mediation. They were trying to cut down costs of litigation, so it was court mediation. This guy came in, he was probably in his late 60’s, and he didn’t have a lot of energy about him so I was thinking that this may not go well. So he came in and I introduced him and started off with a basic question, “What is court mediation?” He says, “Well, (long sigh) that’s kind of a difficult question.” And I just wanted to bang my head on the desk. Here’s a guy who’s an expert on courtroom mediation and he can’t answer the question. Worst interview ever.

Rich: And did you have to go live with that interview? Did it make it on the air?

Rob: It did make it on the air. That was a live interview, so this is what happens when you do it live. Certainly I’ve had plenty of live interviews that were just really bad. Now how do you avoid that pitfall? You do it by pre-interviewing – which we don’t always get to do – and you do it by being very discriminating and trying to always make sure that your interview guest is going to be a good one.

But, can you be sure that you bat 1,000? No. And if you play it safe and conservative and only interview people you know are going to be good, you’re going to miss out on a lot of good interviews, too. So how do you balance that out? I don’t know, it depends on what works for you. That’s something that we wrestle with all the time and there’s no right answer.

Rich: Now you asked me earlier about my dream interview. I’m kind of curious, who out there do you wish you interviewed but just haven’t gotten around to it, whether they are still available or have passed on?

Rob: Well you know what, here’s the thing, Rich. Here’s a story of heartbreak and sadness. I got my dream interview 6 or 7 years ago, I got an interview with Leonard Nimoy, I’m a huge Star Trek fan as you know. The original, classic series. I had seen Leonard Nimoy at an appearance once, and of course I’ve watched him all my life, and I got an interview with Leonard Nimoy. He was appearing at a gallery showing his photos in western Massachusetts.

I was beyond excited. But the only day he could do it was a day in the summer when I had committed to a fundraiser for a museum here in Maine. I was the MC for that fundraiser, they had already printed up promotional material, and they had my name on it. So I could not back out of that commitment which I had already made to doing the fundraiser, and as a result, I missed out on the opportunity to interview Leonard Nimoy. I looked into the possibility of hiring a private plane, I thought it would get me to both places in the same day, but it didn’t work out.

So I had to hand to off to one of my colleague who is a big Star Trek fan, and he did a great job with it. Bu that – honest to God – was one of the scarring, crushing moments of my professional life. Getting Leonard Nimoy, and then not being able to do it.

Rich: Oh, that’s brutal, that breaks my heart. Before we break, do you have any suggestions or anything I haven’t asked you today that would help people become better interviewers? Any tips you’ve learned over the years or mistakes we should avoid?

Rob: You know, so much of it comes down to getting a good person. And then have a conversation with them. Here’s something that people do that I think is a big mistake, they have a notepad in front of them and they look down at their questions and then they look up and ask the subject the question. I almost never now use notes, and sometimes I forget good questions as a result. But I think it has a spontaneous and more natural feel when you talk to someone without notes. And that’s something that a lot of rookies do, they’ve got their yellow legal pad on their knee. Don’t do that. You want to have a spontaneous, lively conversation. That doesn’t matter who you’re talking to. Everyone you’re talking to wants to make a connection with you, so that’s a really important thing.

One other tip I’ll say is it really is useful – this is the oldest thing in the book, its part of storytelling – have a beginning, middle and an end. The middle isn’t as important, the middle is where you can improvise. But have a good idea of how you want the interview to begin and end. How you want it to get going, and then some idea of how you want to wrap it up. It shouldn’t just come to a stop, it’ should have some sort of meaningful closing note that really adds a lot.    

Rich: And that sounds like the perfect way to wrap up today’s interview. Now Rob, you and I have a running joke where you are not the “tech guru”, nor do you pretend to be one on T.V. But yet I’m sure you are online someplace. If people want to check you out, where can they find you online? 

Rob: They can send me an email, I’m at rob.caldwell@wcsh6.com, or you can find the contact information simply by going to wcsh6.com. That is the station’s handy dandy website and you’ll find plenty of information there that will lead you to me. 

Rich: Now you or one of the agents that work there at WCSH has set up a Twitter account for you, is this true?

Rob: That is true. I have a Twitter account, I send out tweets but I don’t – this pains me and I hope my bosses aren’t listening – I never correspond through Twitter. I know, I’m a killjoy, I’m a jerk, it ruins all the fun of it. But I never do any back and forth with people.

Rich: Well I do think that you would enjoy it. If your choice is between talking to people occasionally on Twitter who are going to yell at you for the wrong type of interview, versus taking 12 cross-country trips on your motorcycle, I think the motorcycle wins. So kudos to you, sir.

Rob: Well, that’s a good way to look at it. And this is why I don’t spend a great deal of time on social media, there are just other things I’d rather do. It’s not that I’m a total jerk, it’s just that I’m a partial jerk.

Rich: There you go. Rob, thanks so much for your time today, I really appreciate it.

Rob: My pleasure, thank you, Rich.

Show Notes:

  • You can find Rob online at WCSH’s website, or on Twitter (though he’s not an avid tweeter). He also welcomes your feedback and questions via email at rob.caldwell@wcsh6.com.
  • When Rich Brooks isn’t hard at work at flyte new media, or setting up the next amazing Agents of Change Digital Marketing Conference, he can be found interviewing amazing and informative guests for this podcast, as well as a sought after guest for other industry podcasts.
  • Keep your eyes out for “The Lead Machine”, Rich’s first book which is scheduled to be released in early 2017.